Refine Search
Sort by
823 Chester, Monticello
$219,000
3 Beds ⋅ 2 Baths ⋅ 26022669 MLS
Striking new construction with contemporary architecture, energy-efficient features, and custom finishes throughout. This thoughtfully designed 3-bedroom, 2-bath home offers 1,091 heated and cooled square feet with an open-concept layout, soaring vaulted tongue-and-groove ceilings, and abundant natural light from oversized windows and transom accents. Quartz countertops and custom stained wood cabinetry with soft-close drawers and doors are featured throughout both the kitchen and bathrooms. The kitchen offers stainless steel appliances and overlooks the main living area, creating an ideal space for everyday living and entertaining. Luxury vinyl plank flooring runs throughout the main living areas and bedrooms, while the bathrooms feature tile flooring, full-height tiled tub surrounds, and modern fixtures. Built for efficiency and low maintenance with a standing seam metal roof, tankless water heater, Low-E argon-filled windows, foam and fiberglass insulation, painted white brick exterior, and freshly sodded yard. Refrigerator, washer, and dryer convey. Everything is brand new, offering the opportunity to be the very first owner of this move-in-ready home.

823 Chester, Monticello

Listing courtesy of Trademark Real Estate, Inc..

134 Allen, Monticello
$505,000
4 Beds ⋅ 3 Baths ⋅ 26016002 MLS
This beautiful white two-story traditional home sits on 2.1 acres inside the city limits, but the real standout is the backyard setup. The spacious patio features a brick fireplace and built-in cooking area, creating the perfect spot for entertaining, watching games, or simply relaxing. The property also includes a large detached boat storage shed, along with a two-car carport and an additional two-car carport with storage in between - offering plenty of covered parking and space for equipment or hobbies. Inside, the home offers a functional and comfortable layout with four bedrooms. Upstairs features two bedrooms and one full bath. Downstairs includes the primary bedroom, along with a guest bedroom, a full bath, and an additional half bath for guests. The kitchen opens into the den, creating an easy, connected living space, and you’ll also find a laundry room, a breezeway-style mudroom, and a small bonus room that works well as an office or flex space. If you’ve been looking for space inside and out, with a backyard built for gathering, you’ll want to take a look at this one.

134 Allen, Monticello

Listing courtesy of Trademark Real Estate, Inc..

202 Old Dean, Monticello
$256,000
4 Beds ⋅ 2 Baths ⋅ 26013183 MLS
Custom-Built Country Home on 1.38 Acres with Shop & RV Storage. Discover peaceful country living in this beautifully crafted custom-built home sitting on 1.38 acres of quiet, open land. Designed by a local custom home builder for his own residence, this property blends quality construction with unique flexibility. Inside, the home features two separate living areas, each with two bedrooms, offering the perfect setup for multi-generational living, rental potential, or an easy conversion into a full duplex. One side showcases a modern style, while the other embraces a warm, rustic feel. A handicap-accessible bathroom is located on one side, adding convenience and thoughtful design. Outside, the property includes a large shop ideal for projects, storage, or business use, along with dedicated RV storage—a rare and valuable bonus for travelers or hobbyists.

202 Old Dean, Monticello

Listing courtesy of Monticello Realty.

630 N Main, Monticello
$284,000
5 Beds ⋅ 4 Baths ⋅ 26011368 MLS
Located in the beautiful and historic North Main Street area, this charming home blends timeless character with modern updates, including FRESH EXTERIOR PAINT completed in October 2026! The first two listing photos showcase the fresh new look. Offering 3,784 sq ft, the home features four upstairs bedrooms, the potential for a fifth bedroom downstairs, two full bathrooms with clawfoot tubs, and a half bath. The spacious kitchen, remodeled in 2009, features tile flooring, a work island with seating, and a five-burner gas stove. A majestic staircase leads to the second floor, where you'll find four bedrooms, including the primary suite, also updated in 2009. Additional improvements include a roof replaced in 2018 and downstairs HVAC replaced in 2017 (upstairs unit age unknown). Enjoy the above-ground pool and surrounding deck, perfect for relaxing or entertaining. The property includes two parcels totaling 1.38 acres (MOL). The storage building on the second parcel does not convey. Full of historic charm, spacious living areas, and thoughtful updates, this North Main Street home is a must-see!

630 N Main, Monticello

Listing courtesy of Monticello Realty.

161 Windy Hills, Monticello
$320,000
3 Beds ⋅ 3 Baths ⋅ 26007002 MLS
This beautiful home features natural Arkansas stone siding and offers 3 bedrooms, 2 full baths, and a dedicated office area. The spacious kitchen provides abundant dining space, an in-kitchen bar, and plenty of room for gathering. You’ll enjoy both a formal living area and a large den highlighted by a striking stone fireplace. The property includes a nice 30×30 shop with a 16-ft side shed, perfect for equipment, hobbies, or extra storage. A peaceful pond sits at the front of the property, adding charm and curb appeal, while a back balcony gives you a relaxing place to unwind and take in the wooded views. All of this sits on over four acres of rolling hillside, offering privacy, and the feel of true country living.

161 Windy Hills, Monticello

Listing courtesy of Monticello Realty.

163 Glenwood, Monticello
$215,000
3 Beds ⋅ 2 Baths ⋅ 25041993 MLS
Located in Vivian Manor —a cozy, quiet neighborhood, this home is conveniently situated very close by both local schools, UAM, the square, & all other amenities in Monticello. The property is being sold “as-is, where-is”, & is ready to be customized by a new family to make it their own. The home offers possible flex spaces w/ both a den & formal living area, (used as an office), w/ newer flooring, a kitchen w/ breakfast nook, as well as a formal dining room. 2 bedrooms w/ newer flooring share a hall bath & the primary has an en-suite. The 2 separate backyard areas have potential for many uses like hosting family gatherings, gardening, outdoor storage, & more. The patio is perfect for dining outside or watching the kids & pets play! The concrete area w/ steps leading up was once a pool & is now filled in, but would make a great spot for a fire pit or a reimagined pool/lounge area. The HVAC is 6 yrs old & the fireplace is 3 years old. This home is full of character w/ the unique mansard roof (replaced in ‘23) which frames tall windows, concrete steps lead up to double front doors. The foyer has parquet floors & high ceilings like the formal rooms. Call now to schedule your tour!!!

163 Glenwood, Monticello

Listing courtesy of Monticello Realty.

The data relating to real estate for sale on this web page comes in part from the Internet Data Exchange (IDX) of the Southern Missouri Regional MLS, LLC, Inc. Real estate listings held by Brokerage firms other than our company are marked with the IDX logo and detailed information about them includes the name of the listing Brokers. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The information being provided is not guaranteed, and all information should be verified by the consumer. Any representation that a web site contains all listings shall only mean that the website contains all listing available to the public through the IDX data feed. There may be other properties offered through a REALTOR® that have not been displayed on this site. © 2026 Southern Missouri Regional MLS, LLC. All rights reserved. Last Updated:


SOMO MLS respects the intellectual property rights of others and expects you to do the same. Per the DMCA, SOMO MLS will respond expeditiously to claims of copyright infringement on the Site if submitted to SOMO MLS's Copyright Agent as described below. Upon receipt of a notice alleging copyright infringement, SOMO MLS will take whatever action it deems appropriate within its sole discretion, including removal of the allegedly infringing materials. If you believe that your intellectual property rights have been violated by SOMO MLS or by a third party who has uploaded materials to the Site, please provide the following information to SOMO MLS's designated Copyright Agent listed below: a. A description of the copyrighted work or other intellectual property that you claim has been infringed; b. A description of where the material that you claim is infringing is located on the Site; c. An address, telephone number, and e-mail address where SOMO MLS can contact you and, if different, an e-mail address where the alleged infringing party, if not SOMO MLS, can contact you; d. A statement that you have a good-faith belief that the use is not authorized by the copyright owner or other intellectual property rights owner, by its agent, or by law; e. A statement by you under penalty of perjury that the information in your notice is accurate and that you are the copyright or intellectual property owner or are authorized to act on the owner's behalf; f. Your electronic or physical signature. SOMO MLS may request additional information before removing any allegedly infringing material. In the event SOMO MLS removes the allegedly infringing materials, SOMO MLS will immediately notify the person responsible for posting such materials that SOMO MLS removed or disabled access to the materials. SOMO MLS may also provide the responsible person with your e-mail address so that the person may respond to your allegations. SOMO MLS reserves the right to terminate, limit or suspend any user's access to the Site in the event of repeated infringing activity. If you believe that a user of this Site is a repeat infringer, please follow the above instructions to contact SOMO MLS's Copyright Agent. Please include sufficient information to assist SOMO MLS in determining that the user repeatedly engaged in infringing activity. SOMO MLS registered a designated agent with the Copyright Office pursuant to 17 U.S.C. 512(c). SOMO MLS's designated Copyright Agent is: Laurie Joecks 1310 Primrose, Springfield, MO 65804, Phone: 417-883-1226, Email: laurie@gsbor.com

How much is your home worth?

Get instant property value now!